Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones, and the corresponding alcohols

M. Wakabayashi; H. Wakabayashi; S. Nörenberg; B. Reichardt; K. Kubota; K. H. Engel

doi:10.1021/bk-2012-1098.ch003

Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones, and the corresponding alcohols

M. Wakabayashi
, H. Wakabayashi
, S. Nörenberg
, B. Reichardt
, K. Kubota
, K. H. Engel

Chair of General Food Technology (2008 — 2024)

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution › peer-review

3 Scopus citations

Abstract

Polyfunctional thiols are known to play important roles as aroma compounds owing to their pronounced odor qualities and their low odor thresholds; β-mercaptocarbonyls as well as β-mercaptoalcohols are prominent examples. This chapter describes (i) the enantioseparation of a homologous series of 4-mercapto-2-alkanones and 4-acetylthio-2-alkanones, (ii) the determination of the absolute configurations using a combination of the 1H-NMR anisotropy method and lipase-catalyzed kinetic resolution, (iii) the assessment of the sensory properties of enantiomers by GC/O using a chiral stationary phase, and (iv) the synthesis and the establishment of chromatographic and sensory data on 4-mercapto-2-alkanols and 4-acetylthio-2-alkanols.

Original language	English
Title of host publication	Recent Advances in the Analysis of Food and Flavors
Publisher	American Chemical Society
Pages	27-39
Number of pages	13
ISBN (Print)	9780841227590
DOIs	https://doi.org/10.1021/bk-2012-1098.ch003
State	Published - 2012

Publication series

Name	ACS Symposium Series
Volume	1098
ISSN (Print)	0097-6156
ISSN (Electronic)	1947-5918

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10.1021/bk-2012-1098.ch003

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Wakabayashi, M., Wakabayashi, H., Nörenberg, S., Reichardt, B., Kubota, K., & Engel, K. H. (2012). Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones, and the corresponding alcohols. In Recent Advances in the Analysis of Food and Flavors (pp. 27-39). (ACS Symposium Series; Vol. 1098). American Chemical Society. https://doi.org/10.1021/bk-2012-1098.ch003

@inproceedings{cb741362e6234ac1aa004d0c28c40c57,

title = "Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones, and the corresponding alcohols",

abstract = "Polyfunctional thiols are known to play important roles as aroma compounds owing to their pronounced odor qualities and their low odor thresholds; β-mercaptocarbonyls as well as β-mercaptoalcohols are prominent examples. This chapter describes (i) the enantioseparation of a homologous series of 4-mercapto-2-alkanones and 4-acetylthio-2-alkanones, (ii) the determination of the absolute configurations using a combination of the 1H-NMR anisotropy method and lipase-catalyzed kinetic resolution, (iii) the assessment of the sensory properties of enantiomers by GC/O using a chiral stationary phase, and (iv) the synthesis and the establishment of chromatographic and sensory data on 4-mercapto-2-alkanols and 4-acetylthio-2-alkanols.",

author = "M. Wakabayashi and H. Wakabayashi and S. N{\"o}renberg and B. Reichardt and K. Kubota and Engel, \{K. H.\}",

year = "2012",

doi = "10.1021/bk-2012-1098.ch003",

language = "English",

isbn = "9780841227590",

series = "ACS Symposium Series",

publisher = "American Chemical Society",

pages = "27--39",

booktitle = "Recent Advances in the Analysis of Food and Flavors",

}

Wakabayashi, M, Wakabayashi, H, Nörenberg, S, Reichardt, B, Kubota, K & Engel, KH 2012, Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones, and the corresponding alcohols. in Recent Advances in the Analysis of Food and Flavors. ACS Symposium Series, vol. 1098, American Chemical Society, pp. 27-39. https://doi.org/10.1021/bk-2012-1098.ch003

Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones, and the corresponding alcohols. / Wakabayashi, M.; Wakabayashi, H.; Nörenberg, S. et al.
Recent Advances in the Analysis of Food and Flavors. American Chemical Society, 2012. p. 27-39 (ACS Symposium Series; Vol. 1098).

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution › peer-review

TY - GEN

T1 - Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones, and the corresponding alcohols

AU - Wakabayashi, M.

AU - Wakabayashi, H.

AU - Nörenberg, S.

AU - Reichardt, B.

AU - Kubota, K.

AU - Engel, K. H.

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N2 - Polyfunctional thiols are known to play important roles as aroma compounds owing to their pronounced odor qualities and their low odor thresholds; β-mercaptocarbonyls as well as β-mercaptoalcohols are prominent examples. This chapter describes (i) the enantioseparation of a homologous series of 4-mercapto-2-alkanones and 4-acetylthio-2-alkanones, (ii) the determination of the absolute configurations using a combination of the 1H-NMR anisotropy method and lipase-catalyzed kinetic resolution, (iii) the assessment of the sensory properties of enantiomers by GC/O using a chiral stationary phase, and (iv) the synthesis and the establishment of chromatographic and sensory data on 4-mercapto-2-alkanols and 4-acetylthio-2-alkanols.

AB - Polyfunctional thiols are known to play important roles as aroma compounds owing to their pronounced odor qualities and their low odor thresholds; β-mercaptocarbonyls as well as β-mercaptoalcohols are prominent examples. This chapter describes (i) the enantioseparation of a homologous series of 4-mercapto-2-alkanones and 4-acetylthio-2-alkanones, (ii) the determination of the absolute configurations using a combination of the 1H-NMR anisotropy method and lipase-catalyzed kinetic resolution, (iii) the assessment of the sensory properties of enantiomers by GC/O using a chiral stationary phase, and (iv) the synthesis and the establishment of chromatographic and sensory data on 4-mercapto-2-alkanols and 4-acetylthio-2-alkanols.

UR - https://www.scopus.com/pages/publications/84905574863

U2 - 10.1021/bk-2012-1098.ch003

DO - 10.1021/bk-2012-1098.ch003

M3 - Conference contribution

AN - SCOPUS:84905574863

SN - 9780841227590

T3 - ACS Symposium Series

SP - 27

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BT - Recent Advances in the Analysis of Food and Flavors

PB - American Chemical Society

ER -

Analytical and sensory characterization of chiral 4-mercapto-2-alkanones, 4-acetylthio-2-alkanones, and the corresponding alcohols

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